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Synthesis 2006(18): 3048-3057
DOI: 10.1055/s-2006-950191
DOI: 10.1055/s-2006-950191
PAPER
© Georg Thieme Verlag Stuttgart · New York
Biomimetic Syntheses of Lamellarin and Lukianol-Type Alkaloids
Further Information
Received
22 May 2006
Publication Date:
15 August 2006 (online)
Publication History
Publication Date:
15 August 2006 (online)
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Abstract
The formation of 3,4-diarylpyrrole-2,5-dicarboxylic acids from arylpyruvic acids and 2-arylethylamines was used as a key step for the synthesis of several marine pyrrole alkaloids. The utility of this method is illustrated through the development of syntheses of ningalin B (5), lamellarins G (11a) and K (11b), lukianol A (32), and a lukianol-lamellarin hybrid (24).
Key words
biomimetic synthesis - marine alkaloids - pyrroles - lamellarins - lukianol A
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Compound 17 was prepared from ethyl 3-(4-methoxy-phenyl)pyruvate according to ref. 2b in quantitative yield.